Holiday Rentals in Monticello, NY

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Monticello, NY holiday rentals
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27 Holiday Rentals and Airbnb in Monticello, NY

Best family friendly Monticello, NY holiday rentals

Among the 27 accommodations in Monticello, NY, here are the 4 best family friendly rentals

New! Romantic Agrihood Bungalow Getaway-fireplace/wifi - Monticello, NY
9.8 12 reviews

New! Romantic Agrihood Bungalow Getaway-fireplace/wifi

apartment, South Fallsburg
This South Fallsburg holiday home is situated 3.4km from the Mongaup River and 5km from the Tarry Brae Golf Course, with the Neversink River and The Kartrite Resort & Indoor Waterpark within 14.5km.
The 228 square metre property boasts two bedrooms, one bathroom, sleeps four guests, and includes a swimming pool, terrace, garden, and free Wi-Fi; housekeeping is available on request.
Sunset Estate In The Catskills - Monticello, NY
9.4 71 reviews

Sunset Estate In The Catskills

house, Monticello
Sunset Estate in the Catskills is located in Monticello, New York, just 23 kilometres from the Bethel Woods Center for the Arts and 63 kilometres from Stewart International Airport, offering a peaceful escape from the hustle and bustle of city life. This property has consistently received excellent user ratings for its location, cleanliness, and overall experience.
The villa features seven bedrooms, ideal for large families or groups of friends, and spans 325 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a bar, and parking.
Catskills Lakefront Haven W/ Hot Tub & Game Room - Monticello, NY
9.9 171 reviews

Catskills Lakefront Haven W/ Hot Tub & Game Room

apartment, Monticello
This three-bedroom apartment is situated on Sackett Lake in Monticello, just 145 kilometres from New York City and a short drive from attractions like Holiday Mountain and Bethel Woods. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The property is ideal for families or groups of up to 12 guests, with a spacious layout and modern amenities. Enjoy a private lakeside haven with a hot tub, a wood-burning fireplace, and a fully equipped kitchen, along with kayaks, canoes, and other water sports equipment for exploring the lake.
Starlight Lakehouse; Your Magical 5 Bdrm Getaway! W/ Brand New 7 Seater Hot Tub! - Monticello, NY
9.4 143 reviews

Starlight Lakehouse; Your Magical 5 Bdrm Getaway! W/ Brand New 7 Seater Hot Tub!

apartment, Smallwood
This five-bedroom Smallwood house, sleeping up to 12, boasts a waterfront location with stunning views, less than 10km from the Monticello Casino and Raceway and within 10km of both the Mongaup River and the Forest Reserve at Smallwood.
The property offers a fully equipped kitchen, Jacuzzi, terrace, garden, parking, free Wi-Fi, and an on-site arcade; guests can enjoy fishing, hiking, and various water activities nearby.

Best Monticello, NY holiday rentals with a balcony

Two Bedroom Suite With 2 Queens & 1 King Balcony At The Kartrite Resort! - Monticello, NY
No reviews

Two Bedroom Suite With 2 Queens & 1 King Balcony At The Kartrite Resort!

resort, South Fallsburg
The Kartrite Resort, situated in Thompson, New York, near South Fallsburg, offers the 'Two Bedroom Suite With 2 Queens & 1 King Balcony' and is conveniently located near Bethel Woods Center For The Arts.
This 79 square metre (850 square foot) suite sleeps four, boasting two bedrooms, one bathroom, a well-equipped kitchenette, and access to the resort's extensive amenities including New York's largest water park, multiple pools, restaurants, and a fitness centre.
Close To Trails: Studio W/ Water Views - Monticello, NY
No reviews

Close To Trails: Studio W/ Water Views

apartment, Otisville
This Westbrookville flat offers proximity to nature, being a mere 5-minute walk from Gobbler's Knob State Forest and Sheriff H. Frank Bigger Memorial Park, with Bashakill Vineyards and Otisville Veterans Memorial Park also within 5 kilometres.
This serviced apartment provides internet, a kitchen, air conditioning, a balcony, and barbecue grills, with complimentary self-parking and free WiFi in public areas, and a 10:00 check-out time.
Cozy Cottage W/ Hot Tub!  Family Friendly - Monticello, NY
10 10 reviews

Cozy Cottage W/ Hot Tub! Family Friendly

cottage, Smallwood
This family-friendly cottage in Mongaup Valley, Smallwood, is a 3-minute drive from The Kartrite Resort & Indoor Waterpark and a 5-minute walk from the Mongaup River.
Offering 121 square metres of space for up to six guests, this property features three bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a hot tub, and Wi-Fi, with boating, hiking, and horseback riding available nearby.
Monticello 3-cabin Retreat Near White Lake - Monticello, NY
No reviews

Monticello 3-cabin Retreat Near White Lake

cabin, Smallwood
This four-bedroom holiday home in Mongaup Valley, near White Lake, is situated 9.9 kilometres from Resorts World Catskill and 6.2 kilometres from Bethel Woods Center for the Arts.
This spacious 139 square metre lodge accommodates up to 27 guests with four bedrooms and three bathrooms, offering a swimming pool, terrace, garden, and kitchen facilities including a fridge and microwave oven.

Frequently asked questions about holiday rentals in Monticello, NY

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Best Monticello, NY holiday rentals with a sauna

Outlier Inn Tiny House 1 On Farm Upstate Catskills - Monticello, NY
10 1 review

Outlier Inn Tiny House 1 On Farm Upstate Catskills

apartment, Woodridge
This Woodridge, Upstate New York tiny house, situated 47km from Mohonk Preserve and 35km from Bethel Woods Center for the Arts, offers a convenient base for exploring the Catskills.
This self-catering property sleeps five guests and boasts a fully equipped kitchen, private terrace, air conditioning, parking, a Jacuzzi and sauna.
Spacious Catskills Home With Covered Hot Tub - Monticello, NY
9.8 31 reviews

Spacious Catskills Home With Covered Hot Tub

apartment, Smallwood
This country house in Monticello, Sullivan Catskills, is located 32 kilometres from amenities and offers a secluded rural setting with abundant wildlife, yet is conveniently situated near the Swinging Bridge Reservoir, which permits motorboats.
This expansive 223 square metre residence accommodates up to 10 guests with four bedrooms and three bathrooms, featuring a wood-burning fireplace, an indoor fitness area, multiple outdoor spaces including two decks and a patio, and a fast 240v EV charger available from November 2025.
Luxury Nature Escape | Sauna  Family Friendly - Monticello, NY
10 24 reviews

Luxury Nature Escape | Sauna Family Friendly

apartment, Rock Hill
This Rock Hill mountain property offers ski-in/ski-out access and is located within 5km of Lake Louise Marie, Holiday Mountain Ski and Fun Park, and the Neversink River.
The house, sleeping eight guests in three bedrooms plus a sofa bed, boasts a fully equipped kitchen, two bathrooms, a swimming pool, tennis court, free Wi-Fi, fireplace, on-site arcade, and charcoal grills; ideal for families seeking a self-catering holiday near various attractions.
Spacious Catskills Home With Covered Hot Tub - Monticello, NY
10 1 review

Spacious Catskills Home With Covered Hot Tub

house, Smallwood
This five-bedroom house in Monticello, Catskills, is situated 16km from Bethel Woods Center for the Arts and 69km from Stewart International Airport.
This 194 square metre property boasts three bathrooms, sleeps fifteen guests, includes a jacuzzi, terrace, garden, free Wi-Fi and parking, and offers proximity to fishing, canoeing and hiking opportunities in the Catskills.

Best Monticello, NY holiday rentals with a fireplace

Peaceful Paradise: Dream Holiday Home In Woodridge - Monticello, NY
No reviews

Peaceful Paradise: Dream Holiday Home In Woodridge

apartment, Woodridge
This luxurious six-bedroom, five-bathroom holiday home in Woodridge, New York, is ideally located near Woodridge Trail and Silver Lake, offering easy access to Tarry Brae and Concord Monster Golf Courses.
Sleeping up to sixteen guests, the property boasts a fully equipped kitchen (fridge, microwave), air conditioning, a garden, sauna, parking, internet access, and is pet-friendly, making it perfect for families seeking a relaxing getaway near the Shawangunk Ridge and Roosa Gap State Forests.
Catskills Farmhouse With Above-ground Pool - Monticello, NY
10 3 reviews

Catskills Farmhouse With Above-ground Pool

apartment, Monticello
This rural farmhouse is located in Harris, NY, approximately 24-32 kilometres from Monticello's attractions, offering a peaceful countryside setting with wildlife.
This spacious accommodation for eight guests features a pool table, Pac-Man arcade game, pellet stove, electric fireplaces, a jetted soaker tub, and a back deck with a gas grill, griddle, and outdoor bar.
Catskills Cottage With Lake View Book Now - Monticello, NY
9.9 117 reviews

Catskills Cottage With Lake View Book Now

house, Rock Hill
This Sullivan County villa, situated 31km from Bethel Woods Center for the Arts and 48km from Stewart International Airport, offers a convenient base for exploring the surrounding area.
The recently renovated two-bedroom, one-bathroom property boasts a fully equipped kitchen, free Wi-Fi, private parking, and a relaxing garden, perfect for families or couples seeking a self-catering holiday near Rock Hill, with nearby fishing and hiking opportunities in the Catskills.
Trails Head Tiny House - Monticello, NY
9.7 177 reviews

Trails Head Tiny House

house, Rock Hill
This off-grid tiny home near Rock Hill, New York, is situated approximately 0.16 kilometres from guest parking and provides easy access to the Neversink Unique Area hiking trails.
This solar-powered dwelling, sleeping up to four guests in one bedroom and one bathroom, features a charcoal grill, firepit, and outdoor shower, ideal for nature lovers seeking a unique, secluded getaway near the Neversink River.
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